Diethyl Ether → HCID 67606267, compound

HRID 1619505Notes

Reaction equation

HRID 1619505 reaction equation
C[I:2].[C:3]([O:7][C:8]([NH:10][CH:11]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:12]([O:14][C@@H:15]1[CH:20]2[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]2)[CH2:16]1)=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:29]COCC>C(OCC)(=O)C>[I-:2].[C:3]([O:7][C:8]([NH:10][CH:11]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:12]([O:14][C@@H:15]1[CH:20]2[CH2:21][CH2:22][N+:17]([CH3:29])([CH2:18][CH2:19]2)[CH2:16]1)=[O:13])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 67425060(R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate

Product 1

HCID 67606267HCID 67606267, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl iodide (8.6 μl, 0.14 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate (C1) (50 mg, 0.14 mmol) in ethyl acetate (2 ml), and the reaction was stirred at RT overnight. Et2O (1 ml) was added, and the precipitate was collected by suction filtration and dried under vacuum at 40° C. The product was further purified by preparative HPLC to obtain (3R)-3-(2-(tert-butoxycarbonylamino)-2-phenylacetoxy)-1-methyl-1-azoniabicyclo[2.2.2]octane iodide (24.2 mg; 35% yield).

Workup

  1. filtrationthe precipitate was collected by suction filtration
  2. customdried under vacuum at 40° C
  3. customThe product was further purified by preparative HPLC

Sources & evidence

ORD record
ord-6dae224c017542c98f9cfa03874f2424
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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